Jake Martino is an assassin hired by the Kingpin to kill Spider-Man and his family. When Jake tried shooting Spider-Man from afar, Spidey’s spider-sense kicked in and he was able to dodge in the nick of time, but the bullet hit Aunt May and caused her to go into a coma.
Peter’s not going by his standard rules here and is perfectly willing to kill.
From – Amazing Spider-man Vol. 1 #540